What question did this study set out to answer?

Investigate the reaction mechanisms controlling selective one-electron versus two-electron photoinduced reduction of fullerene C60 using various NADH and NAD dimer analogues.

August 1, 1998Journal of the American Chemical Society

Selective One-Electron and Two-Electron Reduction of C60 with NADH and NAD Dimer Analogues via Photoinduced Electron Transfer

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Authors

SFShunichi FukuzumiKanazawa University TSTomoyoshi SuenobuThe University of Osaka MPMatthias PatzLudwig-Maximilians-Universität München

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Implication

Photochemical study reveals distinct one- and two-electron reduction pathways for C60 using NADH analogues, highlighting tunable electron-transfer mechanisms in organic synthesis.

Key Points

Investigate the reaction mechanisms controlling selective one-electron versus two-electron photoinduced reduction of fullerene C60 using various NADH and NAD dimer analogues.
Irradiated deaerated benzonitrile solutions containing C60 and NADH analogues (BNAH, (BNA)2, t-BuBNAH, or AcrH2) with visible light in the presence or absence of trifluoroacetic acid.
Tracked reaction intermediates and radical ion pairs using laser flash photolysis, measuring quantum yields and kinetic deuterium isotope effects.
Reaction with dimer analogue (BNA)2 achieved selective one-electron reduction to C60•- with a limiting quantum yield exceeding unity (Φ∞ = 1.3) via rapid C-C bond cleavage.
Reaction with t-BuBNAH produced the alkylated anion t-BuC60-, whereas AcrH2 with acid yielded 1,2-C60H2 through sequential electron and proton transfer steps.

Cite This Study

Fukuzumi et al. (1998) studied this question.

synapsesocial.com/papers/6a7086c9f44fa9f079de309a https://doi.org/10.1021/ja9813459

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Implication

Photochemical study reveals distinct one- and two-electron reduction pathways for C60 using NADH analogues, highlighting tunable electron-transfer mechanisms in organic synthesis.

Selective One-Electron and Two-Electron Reduction of C60 with NADH and NAD Dimer Analogues via Photoinduced Electron Transfer

Discussion

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Implication

Key Points

Cite This Study

Selective One-Electron and Two-Electron Reduction of C60 with NADH and NAD Dimer Analogues via Photoinduced Electron Transfer

Discussion

Member takes

Implication

Key Points

Cite This Study

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